Isopropyl iodide → HCID 58934193, compound

HRID 854673Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].[CH:19](I)([CH3:21])[CH3:20].C(OCC)(=O)C>CN(C)C=O>[CH2:7]([O:6][P:4]([CH:9]([CH:19]([CH3:21])[CH3:20])[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

5.5 ml of tert-butyl diethylphosphonoacetate are dissolved in 20 ml of dimethylformamide, and 820 mg of sodium hydride (60% strength in paraffin oil) are added a little at a time at 0° C. The suspension is stirred at 0° C. for 15 minutes, and 2.4 ml of isopropyl iodide are then added. The mixture is stirred at room temperature for 12 hours. 250 ml of ethyl acetate are then added, and the reaction mixture is washed three times with in each case 150 ml of water. The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=5:1. This gives 4.2 g of tert-butyl 2-(diethoxyphosphoryl)-3-methylbutyrate as an oil. C13H27O5P (294.33), MS(ESI): 239 (M-C4H8+H+), Rf(n-heptane:ethyl acetate=1:1)=0.34.

Workup

stirringThe mixture is stirred at room temperature for 12 hours
washthe reaction mixture is washed three times with in each case 150 ml of water
dry with materialThe organic phase is dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue is purified on silica gel using the mobile phase n-heptane

Sources & evidence

ORD record: ord-4193f7a07e4349de9ffa0cfb3ac240a2
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259177B2

Reaction notes

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